Ethyl trifluoroacetate → HCID 136335677, compound

HRID 1170024Notes

Reaction equation

HRID 1170024 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[F:12])[NH:5][C:4](=[O:13])[C:3]=1[C:14]1[NH:18][C:17]2[CH:19]=[C:20]([N:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[CH:21]=[CH:22][C:16]=2[N:15]=1.[F:29][C:30]([F:37])([F:36])[C:31](OCC)=[O:32]>CN(C)C(=O)C>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[F:12])[NH:5][C:4](=[O:13])[C:3]=1[C:14]1[NH:18][C:17]2[CH:19]=[C:20]([N:23]3[CH2:28][CH2:27][N:26]([C:31](=[O:32])[C:30]([F:37])([F:36])[F:29])[CH2:25][CH2:24]3)[CH:21]=[CH:22][C:16]=2[N:15]=1

Participants

4

Reactant 2

HCID 9794Ethyl trifluoroacetateHCID 135543684N-Desmethyl Dovitinib

Product 1

HCID 136335677HCID 136335677, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
130 °C

Procedure

4-Amino-5-fluoro-3-(6-piperazin-1-yl-1H-benzoimidazol-2-yl)-1H-quinolin-2-one was taken up in ethyl trifluoroacetate and N,N-dimethylacetamide (DMA). The resulting solution was heated at 130° C. in a sealed tube for 30 minutes. The reaction was cooled to room temperature and quenched by addition of saturated aqueous sodium bicarbonate followed by pouring the mixture into water. The resulting solid was collected by filtration and washed with diethyl ether to afford 4-amino-5-fluoro-3-{6-[4-(2,2,2-trifluoro-acetyl)-piperazin-1-yl]-1H-benzoimidazol-2-yl}-1H-quinolin-2-one (Rt 2.63 minutes, MH+=457.1), which was immediately taken up in THF. Borane-THF complex (3.3 equivalents) was added and the reaction was stirred at room temperature overnight. After quenching the excess borane with water, the mixture was extracted into ethyl acetate, dried over magnesium sulfate, filtered and concentrated to a brown solid which was purified by reverse phase HPLC to yield the desired compound. MH+=461.1.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customquenched by addition of saturated aqueous sodium bicarbonate
  3. additionby pouring the mixture into water
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with diethyl ether

Sources & evidence

ORD record
ord-f6d5dd4f4f124597a6e5591f9761e73c
Source dataset
uspto-grants-2010_11
Patent number
US07825132B2

Reaction notes

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